Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-((2S,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-((2S,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-2-ylmethyl ester
• CAS No.: 370094-64-7
• Molecular Formula: C₂₆H₃₂O₉S
• Molecular Weight: 520.601

Synonyms:Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-((2S,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-((2S,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-2-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-((2S,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-2-ylmethyl ester

There total 2 articles about Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-((2S,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-2-ylmethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-((2S,3R,4S,5S,6R)-4,5-dihydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-2-ylmethyl ester (370094-61-4) → Toluene-4-sulfonic acid (2R,3R)-3-((2S,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-oxo-3,4-dihydro-2H-pyran-2-ylmethyl ester + Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-((2S,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-2-ylmethyl ester (370094-64-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene;

DOI:10.1021/jo015756a

Reference yield:

Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran-2-ylmethyl ester (222189-65-3) → Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-((2S,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-2-ylmethyl ester (370094-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / HF*Et₃N / acetonitrile / 65 °C

2: 52 percent / Bu₃SnH; AIBN / benzene

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine hydrofluoride; In acetonitrile; benzene;

DOI:10.1021/jo015756a

Reference yield: 28.0%

1-O-acetyl-4-O-(tert-butyldimethyl)silyl-β-L-rhodinose (288859-46-1) + Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-((2S,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-2-ylmethyl ester (370094-64-7) → Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,4R,5R,6R)-4-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester + Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,4R,5S,6R)-5-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester + Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,4R,5R,6R)-4,5-bis-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester

Guidance literature:

With triethylsilyl trifluoromethyl sulfonate; In diethyl ether; at -78 ℃; for 0.25h;

DOI:10.1021/jo015756a

upstream raw materials:

Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-((2S,3R,4S,5S,6R)-4,5-dihydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-2-ylmethyl ester

Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran-2-ylmethyl ester

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